9. How to Talk to Someone Significantly Older or More Experienced Than You Are

So you’re stuck working with a bunch of Old People. It was probably too much to hope that they would hire you and then immediately retire en masse, but having that dream fail to materialize is nevertheless disappointing. It’s not that you have a problem with Old People. Far from it: You know plenty of delightful Old People, and your grandparents have been buying your love for years with that check they send every birthday. It’s that your new colleagues act old, playing it so safe that you wouldn’t be surprised to see training wheels on their weird recumbent bicycles. They wouldn’t know a brilliant new idea if it smacked them in the face. You’re certain of that; you’ve been trying to smack them since day one, and they haven’t even blinked.

Unfortunately, you’re going to be stuck with them for a while. Too many of them have failed to save properly for retirement, and anyway they’re so married to their jobs that they don’t know what they’d do with themselves if they had too much free time. And with all the recent advances in medicine, they might be working right next to you for forever.

You’re welcome to hate these people for the rest of your career. You can complain to your friends about their stodgy ways and shake your head at their stubborn refusal to acknowledge your genius. You can rail against the gross injustice of not being able to run your company five months into your career, and you can excoriate your elders for conspiring in secret to keep you out of the most important conversations. If you wish to work forever in a self-imposed exile, that’s your right.

But in case you want to earn the respect you’re undoubtedly demanding, this chapter describes a step-by-step process to help you bridge the gap between yourself and anyone significantly Older or more experienced than you are.

Step 1: Expect Some Condescension from Them

Nine times out of ten, it won’t be intentional. Yes, you’ll run across the occasional know-it-all braggart, but you can find those people everywhere from age 8 to 88. For the vast majority of your Older colleagues, however, any skepticism or disdain you think they’re throwing at you will be the accidental byproduct of their experience. They like the way they do things because they’ve found success with those strategies, and they’re not immediately going to see any need to do anything differently. Neither would you in their position, and neither do you when someone significantly Younger than you suggests you should change the way you do things. If you interpret their attitude as an attack on you and your ideas, you’ll be setting yourself up for a fight. If instead you realize that they don’t mean to make you feel inferior or unappreciated, you’ll be prepared to establish a strong relationship.

Step 2: Let Them Do Most of the Talking

At least do this at first. Your turn will come. But unless you’ve been hired because of your particular expertise, you have to accept your role as the student. If you allow them to, most of your Older colleagues will be happy to talk about what they do and why they do it that way, partially to initiate you into your company’s culture and partially because all of us like talking about things we understand very well. Establishing yourself as a willing listener is a critical element of any successful relationship, and there will be plenty of time for the inevitable questions and ideas you’ll be stockpiling while you learn how things currently function.

Step 3: Praise Anything You Hear That Sounds Intelligent

If you’ve ever tried teaching a child to play the piano, then you know how frustrating it is to go through a painstaking explanation of chords and scales and melodies only to watch the child ignore everything you’ve said and play whack-a-mole with the keys. In exactly the same way, your Older colleagues will be frustrated if you listen to their explanations about how and why they do things only to start in with your own “new and better” approach. If you can’t find something reasonable, intelligent, shrewd, or eye-opening in the way your company currently operates, then you either haven’t been paying attention or you’ve been hired into the wrong company. The second you let your Older colleagues know that you value what they’ve done, they’ll be prepared to listen to you. Just don’t take this one too far, or you might come off like a brainless brown-noser.

Step 4: Ask a Lot of Questions

If you understand the way your business works and have some ideas about how to improve it, there are basically two ways to go about it: by telling or by asking. Starting out with “I have an idea,” implies that you’ve come up with a foolproof solution to the wealth of inefficiencies your Older colleagues are too blind to see—and it will probably make them slightly defensive. Instead, try something like, “Why are we still advertising on mainstream radio?” or “Has anyone ever conducted a focus group with Latin American families?” This way you can introduce your ideas under the guise of trying to more fully understand how things work. It feels slower, but it will work better—and more quickly—than trying to start at the finish line.

Step 5: Expect Some Frustration

Eventually, if you ask enough questions, you’ll get some pushback. If your Older colleagues are comfortable with the way they do things, they won’t enjoy the implication that there’s something wrong with it. And neither would you, so don’t expect them to be happy with all of your suggestions. The process of consciously incorporating new ideas into our existing framework is always a bumpy one. If you get mad at your Older or more-experienced colleagues for not immediately embracing the wisdom of whatever it is you’re saying, you’ll accomplish nothing.

Step 6: Focus on Improving the Business

Finally, you can act. If you’ve taken all five other steps, you’ve positioned yourself as attentive, thoughtful, and appreciative of many of your Older colleagues’ ideas, and you’ve also asked enough questions that it’s clear you have some ideas of your own. If your 51-year-old team lead is dead set on ignoring everything you have to say, take your ego out of it. Don’t focus on it being your idea; focus on the fact that the idea could save money, eliminate redundancy, or reduce stress. If you’ve asked questions your Older colleagues didn’t know how to answer, point out that their inability to do so is basically the same as admitting that there is a problem (or an opportunity). And if they still don’t listen, find different Older colleagues and repeat the entire process until you get one of them on board. Everything is easier with allies. Is it fun when a 61-year-old chooses only to listen to other 61-year-olds? No, but don’t worry. Everyone will know where the idea came from. Your ego will have its day.

Talking with someone significantly older or more experienced doesn’t have to difficult. It just becomes difficult sometimes because we want things to happen faster than they are likely to. Trust me, I also wish you could start the New York Marathon at mile 25. But I’ve tried, and the police there are just not accommodating.

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